How to Create an Online Holiday Shopping Experience

How to Create an Online Holiday Shopping Experience
Holiday shopping will continue to take place online this year. Here's how to get your site ready for shoppers as customer behavior continues to evolve.
by Stephanie Vozza Oct 25, 2021 — 6 min read
How to Create an Online Holiday Shopping Experience

Many retailers transform their storefronts for the holiday shopping season. Magical-wonderland settings help customers get in the mood for gift-giving. While customers are back to shopping in person in many areas, it’s undeniable that COVID-19 changed customer behavior, and more than ever, people are shopping online. In 2020, retailers using Square Online saw a 29x increase in online orders during the holiday season, compared to 2019. This trend is poised to continue, as customers enjoy the convenience of online ordering, and then enjoy options like delivery, curbside pickup, or buying online and picking up in store (BOPIS).

To adapt, business owners need to rethink how they can develop unique, omnichannel holiday shopping experiences for their customers as they shop online.

While the customer experience is an essential consideration year-round (Gartner defines the term as “the practice of designing and reacting to customer interactions to meet or exceed their expectations, leading to greater customer satisfaction, loyalty, and advocacy.”), during the holidays, a great customer experience is crucial.

If you can create a shopping experience that exceeds customers’ expectations, you’ll become a memorable part of their season. And it will pay off — 84% of companies that prioritize customer experience report an increase in revenue, according to HubSpot.

Here are seven steps that will help you improve your site’s online experience in time for the holidays.

1. Update your design

The first step is to customize your design for the holidays. Take advantage of templates that make this quick and easy. Choose a template that complements your brand, so loyal customers will still recognize the business they know and trust. During the holiday season, shoppers may be browsing several store websites, so you want to grab their attention immediately. You’ve got 15 seconds, which is the average amount of time someone spends on a website before they click elsewhere, according to CrazyEgg.

Use bold, easy-to-read fonts and eye-catching images. To further engage visitors, consider multimedia elements, such as video or interactive features. Another consideration is your use of color.

Red is a holiday color, but it’s also useful in sales. Red creates energy and urgency, and it can make your heart beat faster, according to Kissmetrics research. That’s why it’s often used on a sale sign or call to action on your website. If it works with your logo and branding, consider using it on your homepage and banners.

2. Personalize your customer experience

Customers want to feel valued, and one way you can do that is with personalization. Nearly three-quarters of customers are frustrated by website content that’s not personalized. Using personalization pays off, with an average increase in sales of 19%, according to research from Janrain.

When you personalize an experience for your customers, you increase brand affinity. An easy way to do this is through your email messaging, using the information you gather during sign-ups to address your customer by name.

You can customize promotions and discounts using purchase history data, but email marketing is just the start. Your website can drive sales by using custom content gleaned from customer information, browsing history, and past purchases. A consumer trends report from Kibo found that personalized homepage promotions influence 85% of consumers to buy, while personalized shopping cart recommendations influenced 92% of shoppers online.

3. Make gifting easy

In addition to your regular product categories, consider adding gift sections to your online catalog to help shoppers search for the perfect present. These are also opportunities to take advantage of online holiday shopping trends. For example, you can have them broken down by recipient or price range.

If a shopper needs to purchase a gift within a specific budget, having a page devoted to items you offer that fall within a range can be helpful. And all of us have at least one hard-to-shop-for person on our list. Creating pages that suggest products for people who have specific hobbies or preferences or are within certain demographics can make it easy to find the perfect gift.

Lastly, at checkout, allow customers the option to add a gift message, get a gift receipt, and even pay an optional gift-wrapping fee. This creates a much smoother gift-shopping experience for the customer.

4. Add details and photos to product pages

Be sure to give customers as much product information as possible. If they’re unsure about an item, they’ll likely click away and find something else instead of trying to get answers. Ensure each product has a thorough description that includes dimensions, weight, material, and color options. If possible, add photos that provide a 360-degree view of the item. With the Square Photo Studio App, you can quickly take high-quality photos on your phone showing products from different angles, easily edit out backgrounds (no editing skills required), and post them to your eCommerce site.

5. Highlight gift cards

If you aren’t already offering gift cards on your website, you’re missing out on an essential stream of revenue. Gift cards have been the most popular items on wish lists for more than a dozen years, requested by 59% of those surveyed, according to the National Retail Federation. And shoppers who purchase gift cards buy at least three each holiday season, according to

With supply chain issues and delivery delays plaguing retailers in 2021, gift cards will be more important than ever, particularly for last-minute shoppers. You can offer an eGift card option, a perfect solution for those who waited too long to make their purchase.

Be sure to let customers know about your gift card offerings via email and SMS, particularly as it gets closer to the holidays, even letting customers purchase right then and there using Online Checkout links.

6. Provide clear shipping information

Speedy and reliable shipping is extra-important during the holiday shopping season. This is especially true this year when more shoppers might have to send gifts to loved ones, rather than deliver them in person.

Create a holiday shipping schedule that is posted in a prominent place on your website. For example, set purchase dates that guarantee delivery if sent by standard shipping, two-day shipping, and overnight shipping. Today’s customers expect to receive their purchases fast.

But fast does not mean a more expensive delivery option will do. A recent UPS survey found that holiday shoppers want to find a balance between shipping costs and speed, with cost being the primary concern. In fact, 51% of surveyed shoppers said they would consider a cheaper but slower shipping alternative, with another 38% would want incentives for making that choice.

Shipping costs may vary for you depending on the item, and some items might not shippable to all locales due to local restrictions. You can create custom shipping profiles so that you have more flexibility in what you offer customers.

7. Offer more ways for customers to get their holiday purchases

While customers who shop online overwhelmingly prefer delivery, Square’s 2021 Future of Retail report found that nearly 30% of customers prefer curbside or in-store pickup, with 49% of those shoppers saying it’s because they can get their purchases more quickly. With delivery delays being a real challenge this season, offering options like buy online and pickup in-store (BOPIS) and curbside pick-up makes for a much more convenient customer experience.

With Square for Retail on Square Terminal you can take the customer experience to the next level by making it easier for customers to make additional purchases, obtain a receipt, join a loyalty program, and more – all away from the check out counter. There’s also flexibility in payment options including Afterpay and Cash App, increasing your selling potential.

8. Surprise and delight customers with flash sales and product drops

Flash sales and product drops can drum up a sense of urgency to purchase and excitement about new products. Flash sales allow customers to buy items at a limited-time discount — which is a great way to move extra inventory. Product drops, on the other hand, get customers excited about new products that may only be available in limited quantities. It’s a fun way to test out and introduce new offerings this holiday season. Learn more about how you can schedule item visibility and sale price changes ahead of time through Square Online, and get tips for launching successful flash sales and product drops.

9. Offer great customer service

People make mistakes with online orders, and packages can get lost. Customers will want a way to reach you with their questions. Make sure they have a way to contact you by phone, online chat, or email. Then offer prompt attention. According to a HubSpot Research survey, 90% of consumers want immediate responses from customer support, and 72% define immediate as within 30 minutes. Automated SMS or chatbots can provide a solution here, particularly if you are short-staffed.

By following these seven steps, you can help set up positive online holiday shopping experiences for customers. When you help make a person’s holiday a little brighter, they’ll remember you. A happy customer is more likely to become a loyal customer, and a loyal customer can become an ambassador for your brand, bringing you business during the holidays and beyond.

Stephanie Vozza
Stephanie Vozza is an experienced writer who specializes in small business and retail. She has been a regular columnist for for five years, and her byline has appeared in Inc., Entrepreneur, and Parade.


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